diff --git a/extension/_test/linkify.txt b/extension/_test/linkify.txt
index 134f52b..4791f3c 100644
--- a/extension/_test/linkify.txt
+++ b/extension/_test/linkify.txt
@@ -171,9 +171,23 @@ http://server.intranet.acme.com:1313
 //= = = = = = = = = = = = = = = = = = = = = = = =//
 
 
-17
+18
 //- - - - - - - - -//
 https://g.page/foo
 //- - - - - - - - -//
 <p><a href="https://g.page/foo">https://g.page/foo</a></p>
 //= = = = = = = = = = = = = = = = = = = = = = = =//
+
+
+19: Trailing punctuation (specifically, ?, !, ., ,, :, *, _, and ~) will not be considered part of the autolink
+//- - - - - - - - -//
+__http://test.com/~/a__
+__http://test.com/~/__
+__http://test.com/~__
+__http://test.com/a/~__
+//- - - - - - - - -//
+<p><strong><a href="http://test.com/~/a">http://test.com/~/a</a></strong>
+<strong><a href="http://test.com/~/">http://test.com/~/</a></strong>
+<strong><a href="http://test.com/">http://test.com/</a>~</strong>
+<strong><a href="http://test.com/a/">http://test.com/a/</a>~</strong></p>
+//= = = = = = = = = = = = = = = = = = = = = = = =//
diff --git a/extension/linkify.go b/extension/linkify.go
index 42a87c8..2f046eb 100644
--- a/extension/linkify.go
+++ b/extension/linkify.go
@@ -273,9 +273,20 @@ func (s *linkifyParser) Parse(parent ast.Node, block text.Reader, pc parser.Cont
 		s := segment.WithStop(segment.Start + 1)
 		ast.MergeOrAppendTextSegment(parent, s)
 	}
-	consumes += m[1]
+	i := m[1] - 1
+	for ; i > 0; i-- {
+		c := line[i]
+		switch c {
+		case '?', '!', '.', ',', ':', '*', '_', '~':
+		default:
+			goto endfor
+		}
+	}
+endfor:
+	i++
+	consumes += i
 	block.Advance(consumes)
-	n := ast.NewTextSegment(text.NewSegment(start, start+m[1]))
+	n := ast.NewTextSegment(text.NewSegment(start, start+i))
 	link := ast.NewAutoLink(typ, n)
 	link.Protocol = protocol
 	return link